Welcome to online ecdysteroids database ! . .
Access data · History · Contact

24-EPI-MAKISTERONE A

Year of first isolation: 1985
Formula:C28H46O7
Molecular weight:494
Occurence in plants:
Diploclisia glaucescens [Menispermaceae] » Images of Diploclisia glaucescens Wikipedia: Diploclisia glaucescens [Menispermaceae]
Vitex canescens [Lamiaceae (alt. Labiatae)] » Images of Vitex canescens Wikipedia: Vitex canescens [Lamiaceae (alt. Labiatae)]
Occurence in animals:
Acromyrmex octospinosus [Formicidae] » Images of Acromyrmex octospinosus Wikipedia: Acromyrmex octospinosus [Formicidae]
24-EPI-MAKISTERONE A

STRUCTURE DESCRIPTORS

Canonical SMILESCC(CC(C(C)(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)O)C)C)O)O)O)C(C)(C)O
Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ]
C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](C[C@@H](C(C)(C)O)C)O)O)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-[(2R,3R,5S)-2,3,6-trihydroxy-5,6-dimethylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID12312688
InChiKey
[ ChemIDPlus: search ]
IJRBORPEVKCEQD-TUVIPRGISA-N
InChIInChI=1S/C28H46O7/c1-15(24(2,3)33)11-23(32)27(6,34)22-8-10-28(35)17-12-19(29)18-13-20(30)21(31)14-25(18,4)16(17)7-9-26(22,28)5/h12,15-16,18,20-23,30-35H,7-11,13-14H2,1-6H3/t15-,16-,18-,20+,21-,22-,23+,25+,26+,27+,28+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z495 (M+H)+,
EI-MS m/z (relative intensity %) 
HR-MS 

CARBON NMR

PROTON NMR

C5D5N
0138.1 (t )
0268.1 (d )
0368.1 (d )
0432.5 (t )
0551.4 (d )
06203.3 (s )
07121.6 (d )
08166.1 (s )
0934.6 (d )
1038.7 (s )
1121.2 (t )
1231.8 (t )
1348.2 (s )
1484.2 (s )
1532.1 (t )
1621.6 (t )
1750.1 (d )
1817.9 (q )
1924.5 (q )
2077.1 (s )
2121.4 (q )
2276.2 (d )
2335.3 (t )
2443.5 (d )
2572.3 (s )
2627.0 (q )*
2729.0 (q )*
2816.8 (q )
CD3OD
0137.42
0268.73
0368.54
0432.86
0551.81
06206.44
07122.17
08167.89
0935.14
1039.28
1121.55
1232.50
1349.0*
1485.31
1531.76
1621.62
1750.42
1818.00
1924.39
2078.05
2120.72
2277.83
2335.18
2444.40
2574.06
2625.92
2728.20
2816.85
CD3OD
01-Ha1.43 (dd, 13.3; 12.2)
01-He1.80 (dd, 13.3; 4.4)
02-Ha3.84 (ddd, 12.2; 4.4; 3.2)
03-He3.95 (q, 3; 3; 3)
04-Ha1.71
04-He1.71
05-H2.39 (dd, 12.7; 4.4)
07-H5.81 (d, 2.6)
09-Ha3.15 (ddd, 11.5; 7.0; 2.6)
11-Ha1.71
11-He1.81
12-Ha2.13
12-He1.88
15-Ha1.96
15-Hb1.59
16-Ha1.77
16-Hb2.0
17-H2.38 (dd, 10; 8)
18-Me0.889 (s)
19-Me0.967 (s)
21-Me1.140 (s)
22-H3.48 (dd, 9.5; 2.2)
23-Ha1.86
23-Hb1.06
24-H1.65
26-Me1.189 (s)
27-Me1.193 (s)
28-Me1.034 (s)
D2O
01-Ha1.38
01-He1.88
02-Ha3.99 (m, w1/2 = 22)
03-He4.06 (m, w1/2 = 8)
04-Ha1.75
04-He1.75
05-H2.34 (t )
07-H5.97 (d, 2.5)
09-Ha3.11 (m, w1/2 = 22)
11-Ha1.73
11-He1.85
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H2.34 (m )
18-Me0.87 (s )
19-Me1.00 (s )
21-Me1.22 (s )
22-H3.48 (dd, 11,2)
23-Ha1.85
23-Hb1.00
24-H1.60
26-Me1.16 (s )*
27-Me1.19 (s )*
28-Me1.02 (d, 6.7)

PHYSICAL PROPERTIES

M.P. 
[α]D20 
IR (KBr) ν max (cm-1)3400, 1850
UV (EtOH) λ max (log ε) 

CHROMATOGRAPHY

HPTLC 
TLCSilica plates (EtOAc-95% EtOH 4:1)
GLC 
HPLCNP-HPLC, Column Zorbax-SIL 25 x 0.46 cm, solvent CH2Cl2-iPrOH-H2O 125:25:2, flow-rate 2 ml.min-1, 13.6 min (makisterone A : 16.7 min). RP-HPLC, Column Whatman ODS-2 50 x 0.94 cm, solvent ACN-H2O 1:4, flow-rate 4 ml.min-1.

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 2.2 x 10-7M

REFERENCES

First isolationMILLER, R.W. et al. (1985) Planta Med. 51, 40-42 Search more
GeneralMAURER, P. et al. (1993) Aust. J. Chem. 23, 29-35 Search more
BioactivitiesHARMATHA, J. et al. (1997) Arch. Insect Biochem. Physiol. 35, 219-225 Search more
IdentificationSUKSAMRARN, A. et al. (1997) Phytochemistry 45, 1149-1152 Search more
First isolationLAOSOOKSAHIT, S. et al. (2003) The Journal of KMITNB 13(1), 1-13 Search more
Struct. analysisBUDĚŠÍNSKÝ, M. et al. (2008) Steroids 73, 502-514 Search more

see Important notice
© Université Pierre & Marie Curie, Paris 6, France
© Institute of Organic Chemistry and Biochemistry, Academy of Sciences, Prague, Czech Republic
© Institut National de la Recherche Agronomique, Versailles, France
designed by Cybersales a.s.
Powered by Cybersales
PRINTER READY | MEDIUM | WIDE